5 years ago

Ring Opening of Epoxides Induced by Pentaphenylborole

Ring Opening of Epoxides Induced by Pentaphenylborole
Sam Yruegas, Jason L. Dutton, Caleb D. Martin, Charles Wilson
The unsaturated antiaromatic BC4 heterocycle pentaphenylborole has been shown to have diverse reactivity with a variety of substrates, including the insertion of polar functional groups into the ring as a route to conjugated boracycles. This work investigates the reactivity of a selection of epoxides with pentaphenylborole, both computationally and experimentally, revealing that the substitution is highly influential on the reaction outcome. Specifically, isobutylene oxide results in protodeborylation to a borabutadiene chain attributed to the acidic β-hydrogen atoms, 1,1-diphenylethylene oxide inserts the C2O unit to furnish a BOC6 heterocycle, and cyclohexene oxide inserts two epoxides to form an unusual BC8O2 ring. The last two species represent rare boron-containing rings of eight atoms or greater, with the 11-membered species being only the second reported and the first crystallographically characterized.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00152

DOI: 10.1021/acs.organomet.7b00152

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